1. Field of the Invention
This invention relates to a new process for the preparation of novel substituted N-alkoxy-N-substituted-2,6-dinitroanilines.
2. Description of the Prior Art
Various 2,6-dinitroanilines have been described in the chemical literature. Hantzsch, Deutsche Chemische Gesellschaft Berichte, 43, 1662-1685 (1910) discloses N,N-dipropyl-4-methyl-2,6-dinitroaniline and N,N-dimethyl-4-methyl-2,6-dinitroaniline. Joshi et al., C. A. 28, 469 (1934) disclose N,N-dimethyl-4-iodo-2,6-dinitroaniline, N,N-dimethyl-4-bromo-2,6-dinitroaniline, 4-iodo-2,6-dinitrophenylpiperidine, and 4-bromo-2,6-dinitrophenylpiperidine. Borsche et al., C. A. 5, 2079 (1911) disclose 2,6-dinitrophenylpiperidine. Daudt et al. U.S. Pat. No. 2,212,825, disclose a number of 2,6-dinitroanilines bearing a trifluoromethyl group in the 4-position. The preparative methods described in the above references are completely different from the novel method disclosed and claimed in the instant application.
The utility of 2,6-dinitroanilines in agriculture was first disclosed in Soper, U.S. Pat. Nos. 3,111,403; 3,257,190; 3,332,769; and 3,367,949. Soper disclosed such compounds to possess herbicidal activity, notably preemergent herbicidal activity. Following Soper, a large number of related dinitroanilines have also been shown to possess similar herbicidal activity. See, for example, U.S. Pat. Nos. 3,321,292; 3,617,251; 3,617,252; 3,672,864; 3,672,866; 3,764,624; and 3,877,924 and Belgian Pat. No. 787,939. The methods of preparing the 2,6-dinitroanilines disclosed in the references as cited in this paragraph are also different from the novel process disclosed and claimed in the instant aplication.